152-97-6 Usage
Description
Fluocortolone is a glucocorticoid, a class of steroid hormones that are naturally produced in the adrenal cortex. It is structurally similar to Fluocortin, but with one less keto group. This pale yellow solid is known for its anti-inflammatory and immunosuppressive properties, making it a valuable compound in the medical field.
Uses
Used in Pharmaceutical Industry:
Fluocortolone is used as an anti-inflammatory agent for the treatment of various conditions characterized by inflammation, such as hemorrhoids. Its glucocorticoid nature allows it to effectively reduce inflammation and alleviate symptoms associated with these conditions.
Additionally, due to its immunosuppressive properties, Fluocortolone can be used as an immunosuppressant in the treatment of autoimmune diseases and conditions that require modulation of the immune system. This application helps in managing the immune response and preventing further damage to the body's tissues.
Originator
Ultralan,Schering,W. Germany,1965
Manufacturing Process
(a) 16α-Methyl-6α-Fluoro-δ4-11β,21-Diol-3,20-Dione:16α-methyl-6α-fluoro-δ4-
pregnene-21-ol-3,20-dione-21-acetate (MP 132°/134° to 138°C, UVε238=
15,000) is hydroxylated with Curvularia lunata in 11β-position using the
fermentation method whereby the 21-acetate group is simultaneously
saponified. The hitherto unknown starting material 16α-methyl-6α-fluoro-δ4-
pregnene-21-ol-3,20-dione-21-acetate is obtained from 16α-methyl-δ5-
pregnene-3β,21-diol-20-one-21-acetate, MP 152° to 154°C, by the addition of
bromofluorine (from N-bromoacetamide and hydrogen fluoride) onto the 5-6
double bond, oxidation of the 3β-hydroxyl group with chromic acid,
introduction of the δ4-double bond by splitting of the hydrogen bromide and
acid isomerization of the 6β-fluoro substituent to the 16α-methyl-6α-fluoro-δ4-
pregnene-21-ol-3,20-dione-21-acetate. By chromatographic purification on
silica gel the 16α-methyl-6α-fluoro-δ4-pregnene-11β,21-diol-3,20-dione is: MP
166°/167° to 171°C.(b) 16α-Methyl-6α-Fluoro-δ4-Pregnene-11β,21-Diol-3,20-Dione-21-Acetate:By
reaction of the compound of (a) with acetic anhydride in pyridine at room
temperature, the acetate is obtained and recrystallized from ethyl acetate, MP
248°/249° to 251°C.(c) 16α-Methyl-6α-Fluoro-δ1,4-Pregnadiene-11β,21-Diol-3,20-Dione:16α-
methyl-6α-fluoro-δ4-pregnene-11β,21-diol-3,20-dione is dehydrogenated with
Corynebacterium simplex. The extraction residue is subjected to
chromatography on silica gel and after recrystallization there is obtained from
methylene chloride-isopropyl ether 16α-methyl-6α-fluoro-δ1,4-pregnadiene-
11β,21-diol-3,20-dione, MP 180°/181° to 182°C.
Therapeutic Function
Glucocorticoid
Flammability and Explosibility
Notclassified
Check Digit Verification of cas no
The CAS Registry Mumber 152-97-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,5 and 2 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 152-97:
(5*1)+(4*5)+(3*2)+(2*9)+(1*7)=56
56 % 10 = 6
So 152-97-6 is a valid CAS Registry Number.
InChI:InChI=1/C22H29FO4/c1-11-6-14-13-8-16(23)15-7-12(25)4-5-21(15,2)20(13)17(26)9-22(14,3)19(11)18(27)10-24/h4-5,7,11,13-14,16-17,19-20,24,26H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19-,20-,21+,22+/m1/s1
152-97-6Relevant articles and documents
Preparation of 6-alpha-fluoro-11-beta, 21-dihydroxy-16-alpha-methyl-1,4-pregnadiene-3, 20-dione (fluocortolone) via substrate-structure-directed specific 11-beta-hydroxylation by Curvularia lunata
Kieslich,Petzoldt,Kosmol,Koch
, p. 168 - 176 (1969)
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Method for reducing or preventing transplant rejection in the eye and intraocular implants for use therefor
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, (2008/06/13)
Methods for reducing or preventing transplant rejection in the eye of an individual are described, comprising: a) performing an ocular transplant procedure; and b) implanting in the eye a bioerodible drug delivery system comprising an immunosuppressive agent and a bioerodible polymer.
